S-15183a
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03395 |
| CAS | |
| Molecular Weight | 416.5 |
| Molecular Formula | C25H36O5 |
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Description
S-15183a is a sphingosine kinase inhibitor produced by Zopfiella inermis SANK 15183. It inhibited sphingosine kinase from rat liver with IC50 value of 2.5 µmol/L. It also inhibited endogenous SPH kinase activity in intact platelets.
Specification
| Synonyms | S-15183 a |
| IUPAC Name | (3-heptyl-7-methyl-6,8-dioxoisochromen-7-yl) octanoate |
| Canonical SMILES | CCCCCCCC1=CC2=CC(=O)C(C(=O)C2=CO1)(C)OC(=O)CCCCCCC |
| InChI | InChI=1S/C25H36O5/c1-4-6-8-10-12-14-20-16-19-17-22(26)25(3,24(28)21(19)18-29-20)30-23(27)15-13-11-9-7-5-2/h16-18H,4-15H2,1-3H3 |
| InChI Key | YMXPNDJGGNEMOH-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Oily Matter |
Reference Reading
1. S-15183a and b, new sphingosine kinase inhibitors, produced by a fungus
K Kono, M Tanaka, Y Ono, T Hosoya, T Ogita, T Kohama J Antibiot (Tokyo). 2001 May;54(5):415-20. doi: 10.7164/antibiotics.54.415.
In the course of our screening for inhibitors of sphingosine kinase, we found two active compounds in a culture broth of a fungus, Zopfiella inermis SANK 15183. The structures of the compounds, named S-15183a and b, were elucidated by a combination of spectroscopic analyses to be new azaphilone-type metabolites. S-15183a and b inhibited sphingosine kinase from rat liver with IC50 values of 2.5 and 1.6 microM, respectively. S-15183a also inhibited endogenous SPH kinase activity in intact platelets.
2. Synthesis of the azaphilones using copper-mediated enantioselective oxidative dearomatization
Jianglong Zhu, Nicholas P Grigoriadis, Jonathan P Lee, John A Porco Jr J Am Chem Soc. 2005 Jul 6;127(26):9342-3. doi: 10.1021/ja052049g.
An approach to the asymmetric synthesis of the azaphilone natural products is reported involving copper-mediated enantioselective oxidative dearomatization of o-alkynylbenzaldehydes. The approach was successfully applied to the synthesis of (-)-S-15183a and several unnatural azaphilones.
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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